CN109679371A - A kind of preparation method of aqueous food grade pigment PR49:1 - Google Patents
A kind of preparation method of aqueous food grade pigment PR49:1 Download PDFInfo
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- CN109679371A CN109679371A CN201910041621.7A CN201910041621A CN109679371A CN 109679371 A CN109679371 A CN 109679371A CN 201910041621 A CN201910041621 A CN 201910041621A CN 109679371 A CN109679371 A CN 109679371A
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- 239000000049 pigment Substances 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 235000013305 food Nutrition 0.000 title claims abstract description 18
- 238000005859 coupling reaction Methods 0.000 claims abstract description 32
- 239000007788 liquid Substances 0.000 claims abstract description 23
- 230000008878 coupling Effects 0.000 claims abstract description 19
- 238000010168 coupling process Methods 0.000 claims abstract description 19
- 239000012860 organic pigment Substances 0.000 claims abstract description 18
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 17
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 claims abstract description 11
- SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 9
- 238000012805 post-processing Methods 0.000 claims abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 61
- 150000005004 2-naphthylamines Chemical class 0.000 claims description 29
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 21
- 238000003756 stirring Methods 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 14
- KSTGSVANFMJGGB-UHFFFAOYSA-N 2-ethylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(CC)=CC=C21 KSTGSVANFMJGGB-UHFFFAOYSA-N 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 claims description 9
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 8
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 8
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 8
- 235000010288 sodium nitrite Nutrition 0.000 claims description 7
- 238000012360 testing method Methods 0.000 claims description 7
- 238000010792 warming Methods 0.000 claims description 6
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 claims description 5
- 229910001626 barium chloride Inorganic materials 0.000 claims description 5
- 238000005352 clarification Methods 0.000 claims description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000013049 sediment Substances 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 238000012790 confirmation Methods 0.000 claims description 2
- 238000001514 detection method Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 claims 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims 1
- 238000005259 measurement Methods 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 239000006228 supernatant Substances 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 5
- 238000000034 method Methods 0.000 description 11
- 239000013078 crystal Substances 0.000 description 9
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- 241001062009 Indigofera Species 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 230000009514 concussion Effects 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000005002 naphthylamines Chemical class 0.000 description 1
- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- -1 quinone hydrazone Chemical class 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B63/00—Lakes
- C09B63/005—Metal lakes of dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0014—Monoazo dyes prepared by diazotising and coupling from diazotized aminonaphthalene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/103—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the naphthalene series
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/103—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the naphthalene series
- C09B29/106—Hydroxy carboxylic acids of the naphthalene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
A kind of preparation method of the red 49:1 of aqueous food grade organic pigment, belong to aqueous food grade organic pigment field, preparation method includes the preparation of diazo liquid, the preparation of material liquid, coupling reaction, color lakeization reaction and post-processing, the second diazo component 2 naphthylamine 6 sulfonic acid is added in the preparation step of diazo liquid, the second coupling component 1- hydroxy-2-naphthoic acid and aqueous pigment modifying agent is added in the preparation step of coupling solution, the obtained red 49:1 of aqueous food grade organic pigment, with lower viscosity and higher tinting strength, tinting power and glossiness, and have excellent storage stability.
Description
Technical field
The invention belongs to aqueous foods to pack organic field of pigments, be related to the preparation of aqueous food grade pigment PR49:1 a kind of
Method.
Background technique
Currently, aqueous food grade pigment red 4 9:1 is widely used in aqueous color paste system, belong to the organic face of azo lake class
Material, the kind are barium salt color lake, provide neutral red, the existing preparation process of pigment red 4 9:1 is mostly: by 2- naphthylamines -1- sulfonic acid
It is dissolved in sodium hydroxide solution, adds hydrochloric acid acid out, sodium nitrite solution is then added dropwise, reacted 1 hour, obtain diazonium
Liquid；Ethyl naphthol is dissolved to obtain coupling solution with sodium hydroxide solution；And the coupling manner being just coupled all is taken, reaction is finished, and is added
Enter barium chloride solution and carry out color lakeization reaction, is finally filtered, washing, dry pigment red 4 9:1.But above-mentioned preparation method
Viscosity is high when the pigment red 4 9:1 of production is applied in an aqueous medium, and tinting strength, tinting power is low, and mass color is poor, especially poor storage stability,
It is easy to swell.
Organic pigment solid solution (or mixed crystal method, Mixed Crystal) method is that widely applied organic pigment is modified
Method.Wang Deyun etc. describe red azo mordant pigment crystal form and surface treatment method (dye industry, 1995,3 (32):
14-21)；The synthetic method of pigment red 4 9:1 a kind of is described in patent CN201210358115.9, method is addition second
Diazonium salt component 2- naphthylamines -1,5- disulfonic acid and nonionic surfactant, while in coupling reaction, 2- hydroxyl -3- is added
Polyoxyalkyl amine modifying agent and the examination of chlorination aluminum lakeization is added in color lakeization reaction as the second coupling component in naphthoic acid
Agent.
Summary of the invention
The present invention provides the preparation methods of red 49:1 of aqueous food grade organic pigment a kind of, to solve prior art production
Pigment red 4 9:1 when applying in an aqueous medium existing viscosity it is higher, tinting strength, tinting power is low, and glossiness is poor, and especially storage is steady
Qualitative difference, is easy the problem of swelling.
The present invention realizes its goal of the invention, and used technical solution is:
The second diazo component 2- is added in the preparation method of the red 49:1 of aqueous food grade organic pigment in the preparation of diazo liquid
Component 1- hydroxy-2-naphthoic acid and Winsperse5320 is added in coupling solution preparation in naphthylamines -6- sulfonic acid.
Specific preparation method, includes the following steps:
(1) diazotising
By 2- naphthylamines -1- sulfonic acid (tobias acid) and the second diazo component 2 naphthylamine 6 sulfonic acid, it is dissolved in sodium hydrate aqueous solution
In, pH=8.5-9 is measured, stirs and checks dissolved clarification；0-5 DEG C is cooled to, hydrochloric acid acid out is added, is stirred, confirmation acid out is uniform；It will
Sodium nitrite in aqueous solution was added in 30 minutes, carried out diazo-reaction, and stirring is micro- blue when the detection of KI test paper, obtained weight
Nitrogen liquid, it is spare.
The molar ratio of 2- naphthylamines -1- sulfonic acid (tobias acid) and sodium hydroxide is 1:1.06-1.08.
The molar ratio of sodium hydroxide and 2- naphthylamines -1- sulfonic acid (tobias acid) is 1.06-1.08:1；
The molar ratio of 2 naphthylamine 6 sulfonic acid and 2- naphthylamines -1- sulfonic acid (tobias acid) is 0.002-0.004:1；
The molar ratio of hydrochloric acid and 2- naphthylamines -1- sulfonic acid (tobias acid) is 2.3-2.5:1；
The molar ratio of sodium nitrite and 2- naphthylamines -1- sulfonic acid (tobias acid) is 1.002-1.004:1.
(2) preparation of material liquid
Sodium hydroxide is added to the water, then heating stirring makes it completely dissolved, then ethyl naphthol and second is added thereto
Coupling component 1- hydroxy-2-naphthoic acid and the Winsperse5320 dissolved, stirring and dissolving obtain coupling solution；
The sodium hydroxide and ethyl naphthol molar ratio is 1.3-1.5:1；
The 1- hydroxy-2-naphthoic acid and ethyl naphthol molar ratio is 0.05-0.07:1；
Wherein aqueous pigment modifying agent is Winsperse5320 (molecular weight ranges 600-18000000)
Wherein aqueous pigment modifying agent additional amount is the 3%-8% of gained pigment weight.
(3) coupling reaction
Diazo liquid made from step (1) is added in above-mentioned material liquid and carries out coupling reaction, the time is 10-30 points
Clock, coupling finish, and adjust pH=9.5-10 with sodium hydroxide, obtain coupling reaction liquid；Water is added in sodium hydroxide at the same time
In, rising temperature for dissolving, then rosin is added thereto, stirring checks dissolved clarification to dissolving；Rosin liquid is added in coupling reaction liquid,
Obtain pigment suspension；
Wherein rosin and 2- naphthylamines -1- sulfonic acid molar ratio are 0.5:1.
(4) color lakeization is reacted
Agent barium chloride in color lake is added into above-mentioned pigment suspension and carries out color lakeization reaction, stirs 60 minutes, fills it
Color separation is formed sediment, and is warming up to 85 DEG C, keeps the temperature 30 minutes, adjusts pH=8.5；
(5) it post-processes
The product filtering that step (4) is obtained, rinses, dries, crush, can be obtained aqueous food grade pigment red 4 9:1 at
Product.
Compared with prior art, beneficial effects of the present invention are as follows:
(1), the present invention prepares the method for organic pigment " mixed crystal " using more diazo components and more coupling components to prepare
PR49:1, but be different from described in the patent application document application No. is CN201210358115.9 recorded in background technique
2- naphthylamines -1,5- disulfonic acid is introduced in 2- naphthylamines -1- sulfonic acid diazo component to prepare organic pigment mixed crystal, the present invention is using knot
Structure only has a sulfonic 2 naphthylamine 6 sulfonic acid mix preparing mixed crystal with 2- naphthylamines -1- sulfonic acid.Using 2- naphthylamines-
1,5- disulfonic acid forms sediment to prepare organic pigment colour, because possessing sulfonic groups more more than body pigment structure in its structure,
When middle color lake agent carries out color lake, nucleus formation in color lake is slower, and crystalline pigment growth is uneven, and pigment mixed crystal can be easily separated
(body pigment component is separated with group is mixed)；And use the isomer 2- naphthalene of main body diazonium structure (2- naphthylamines -1- sulfonic acid)
Amine -6- sulfonic acid is come when preparing mixed crystal, because of its water-soluble and color lake nucleus formation speed similar with body pigment structure, formation
Mixed crystal is uniform.
(2) in coupling component, ethyl naphthol is mixed using 2,3- acid, the organic pigment prepared exists as follows
Azo and the interconversion of quinone hydrazone, wherein hydroxyl more participates in intramolecular and forms hydrogen bond (reaction equation 1)；
And when carrying out coupling reaction using 1- hydroxyl -2- naphthoic acid, the hydroxyl on No. 4 positions, No. 1 position occurs for coupling not
Intramolecular hydrogen bond can be formed, mainly forms intermolecular hydrogen bonding (reaction equation 2) with other pigment molecules.Stronger molecule between pigment
Between hydrogen bond so that pigment particles structure is finer and close, when carrying out mill base grinding and dispersion, viscosity is smaller.
Be as the advantage of auxiliary agent using Winsperse5320: it can participate in coupling reaction, become the one of pigment molecule
Part will not fall off from surface of pigments, and modified pigment has better dispersion performance, storage stability in water-based system.
(3) pigment red 4 9:1 prepared by the present invention has lower viscosity and higher tinting strength, tinting power and glossiness, especially
With better storage stability.
Specific embodiment
Illustrate technical solution of the present invention below with reference to specific embodiment:
Embodiment 1:
(1) preparation of diazo liquid
In diazo-reaction kettle be added water 1000L, be added with stirring 100Kg (technical grade, 98%, about 0.439 ×
103Mol) 2- naphthylamines -1- sulfonic acid (tobias acid) and 0.3Kg (technical grade, 98%, about 0.00132 × 103Mol) the second diazo component
2 naphthylamine 6 sulfonic acid, is added sodium hydroxide (concentration 30%) 64-65Kg, pH value 7.5-8, and dissolution is cooled to 0 DEG C, adds
130Kg hydrochloric acid (concentration 30%) is acidified, and by 31Kg (being made into 30% solution of concentration) sodium nitrite, interior be added of 30min is carried out
Diazo-reaction, stirs 60 minutes by 5-10 DEG C of temperature, until the micro- indigo plant of KI test paper, wait be coupled.
Wherein sodium hydroxide and 2- naphthylamines -1- sulfonic acid molar ratio are 1.08:1；
2 naphthylamine 6 sulfonic acid and 2- naphthylamines -1- sulfonic acid molar ratio are 0.003:1；
Hydrochloric acid and 2- naphthylamines -1- sulfonic acid molar ratio are 2.38:1；
Sodium nitrite and 2- naphthylamines -1- sulfonic acid molar ratio are 1.003:1.
(2) preparation of material liquid
Add 85Kg (30%) sodium hydroxide in 800L water, 60 DEG C is warming up to, by 67.2Kg (98%) ethyl naphthol and 5Kg second
It is coupled component 1- hydroxy-2-naphthoic acid to be added, is allowed to be completely dissolved, the aqueous pigment modifying agent dissolved is added
Winsperse5320 8Kg, adjustment volume be 3200L, 10 DEG C of temperature.
Ethyl naphthol and 2- naphthylamines -1- sulfonic acid molar ratio are 1.025:1；
1- hydroxy-2-naphthoic acid and 2- naphthylamines -1- sulfonic acid molar ratio are 0.059:1；
Anion-polyacrylamide Winsperse5320 additional amount is the 3.33% of gained pigment dry weight；
The molar ratio of sodium hydroxide and ethyl naphthol is 1.39:1.
(3) coupling reaction
Positive coupling: diazo liquid is added in coupling solution in 30 minutes under stirring and is coupled, pH=9.5-10, temperature is not
More than 10 DEG C, the micro- excess of ethyl naphthol is stirred 30 minutes, pH=9.5-10；60Kg rosin soap solution is added (to be added in 180L water
30Kg (30%) sodium hydroxide, heat up 90-95 DEG C, by 60Kg rosin addition be warming up to boiling make it dissolve it is transparent), stir 30 points
Clock, pH=10-10.5.
Wherein rosin and 2- naphthylamines -1- sulfonic acid molar ratio are 0.5:1.
(4) color lakeization is reacted
100Kg (98%) barium chloride is added in 350L water, 60 DEG C is warming up to, is allowed to be completely dissolved, be added to coupling bucket
In, pH=9-9.5 is stirred 60 minutes, is warming up to 85 DEG C, keeps the temperature 30 minutes, adjusts pH=8.5；
Wherein barium chloride and 2- naphthylamines -1- sulfonic acid molar ratio are 1.05:1.
(5) it post-processes: filtering, washing, dry the red 49:1 of 240Kg aqueous food grade organic pigment at 85 DEG C.
Embodiment 2:
2 difference from Example 1 of embodiment is:
In the preparation step of material liquid: the additional amount of aqueous pigment modifying agent is 13Kg, is gained pigment dry weight
5.4%.
Embodiment 3:
3 difference from Example 1 of embodiment is:
In the preparation step of material liquid: the additional amount of aqueous pigment modifying agent is 18Kg, is gained pigment dry weight
7.5%.
The sample of 4 embodiment 1-3 of embodiment is applied to detect in aqueous ink
By 17.5 parts of the resulting pigment of embodiment 1-3,32.5 parts of aqueous promoter, the drop of defoaming agent two and 50 parts of bead are adopted
With concussion instrument, said mixture is dispersed 60 minutes to get aqueous ink.It is carried out with BrookFieldDV-II type viscosimeter aqueous
Black viscosity test；Slurry is scratched on drawdown sheet with No. 10 silk sticks, carries out glossiness test with Grossmeters, with colour photometer into
The test of row tinting strength, tinting power.It tests compared with acquired results are compared with the red 49:1 product of existing organic pigment as shown in table 1:
Table 1.
Claims (5)
1. a kind of preparation method of the red 49:1 of aqueous food grade organic pigment, which is characterized in that is added in the preparation of diazo liquid
Two diazo component 2 naphthylamine 6 sulfonic acids, coupling solution preparation in be added second coupling component 1- hydroxy-2-naphthoic acid and
Winsperse5320；
The molar ratio of 2 naphthylamine 6 sulfonic acid and 2- naphthylamines -1- sulfonic acid is 0.003:1；
The molar ratio of 1- hydroxy-2-naphthoic acid and ethyl naphthol is 0.06:1；
Winsperse5320 molecular weight is 600-18000000, and dosage is the 3%-8% for accounting for total pigment weight；
The following steps are included:
(1) preparation of diazo liquid
2- naphthylamines -1- sulfonic acid and the second diazo component 2 naphthylamine 6 sulfonic acid are dissolved in sodium hydrate aqueous solution, measurement pH=
8.5-9, stirring, and check dissolved clarification；0-5 DEG C is cooled to, hydrochloric acid acid out is added, stirring confirmation acid out is uniform；By sodium nitrite water
Solution was added in 30 minutes, carried out diazo-reaction, and stirring is micro- blue when the detection of KI test paper, obtains diazo liquid, spare；
The preparation of material liquid
Sodium hydroxide is added to the water, heating, stirring make it completely dissolved, and ethyl naphthol and the second coupling component 1- are added thereto
Hydroxy-2-naphthoic acid stirs dissolved clarification, adds the aqueous pigment modifying agent dissolved, obtain coupling solution；
Coupling reaction
Diazo liquid made from step (1) is added in above-mentioned material liquid and carries out coupling reaction, the time is 10-30 minutes, even
Conjunction finishes, and with sodium hydroxide tune pH=9.5-10, obtains coupling reaction liquid；Sodium hydroxide is added to the water at the same time, is heated up molten
Solution, then rosin is added thereto, stirring checks dissolved clarification to dissolving；Rosin liquid is added in coupling reaction liquid, it is outstanding to obtain pigment
Supernatant liquid；
Color lakeization reaction
Agent barium chloride in color lake is added into above-mentioned pigment suspension and carries out color lakeization reaction, stirs 60 minutes, makes its abundant color
It forms sediment, is warming up to 85 DEG C, keep the temperature 30 minutes, adjust pH=8.5；
Post-processing
The product filtering that step (4) is obtained, rinses, dries, crush, aqueous food grade pigment red 4 9:1 finished product can be obtained.
2. the preparation method of the red 49:1 of aqueous food grade organic pigment described in claim 1, which is characterized in that in step (1),
The molar ratio of 2- naphthylamines -1- sulfonic acid and sodium hydroxide is 1:1.06-1.08；
The molar ratio of sodium hydroxide and 2- naphthylamines -1- sulfonic acid is 1.06-1.08:1；
The molar ratio of 2 naphthylamine 6 sulfonic acid and 2- naphthylamines -1- sulfonic acid is 0.002-0.004:1；
The molar ratio of hydrochloric acid and 2- naphthylamines -1- sulfonic acid is 2.3-2.5:1；
The molar ratio of sodium nitrite and 2- naphthylamines -1- sulfonic acid is 1.002-1.004:1.
3. the preparation method of the red 49:1 of aqueous food grade organic pigment described in claim 1, which is characterized in that in step (2)
The sodium hydroxide and ethyl naphthol molar ratio is 1.3-1.5:1；
The 1- hydroxy-2-naphthoic acid and ethyl naphthol molar ratio is 0.05-0.07:1.
4. the preparation method of the red 49:1 of aqueous food grade organic pigment described in claim 1, which is characterized in that aqueous pigment changes
Property agent additional amount be gained pigment weight 3%-8%.
5. the preparation method of the red 49:1 of aqueous food grade organic pigment described in claim 1, which is characterized in that aqueous pigment changes
Property agent be Winsperse5320, molecular weight ranges 600-18000000.
Priority Applications (1)
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| CN113698792A (en) * | 2021-09-10 | 2021-11-26 | 百合花集团股份有限公司 | Preparation method of azo lake organic pigment capable of reducing aromatic amine residues |
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| JP2003155421A (en) * | 2001-11-21 | 2003-05-30 | Toyo Ink Mfg Co Ltd | Method for producing azo pigment and azo pigment to be obtained thereby |
| CN102585546A (en) * | 2011-12-30 | 2012-07-18 | 山东宇虹颜料有限公司 | Preparation method for C.I. pigment red 53:1 |
| CN102838883A (en) * | 2012-09-25 | 2012-12-26 | 山东宇虹新颜料股份有限公司 | Preparation method for C.I. paratonere 49:1 |
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|---|---|---|---|---|
| JP2003155421A (en) * | 2001-11-21 | 2003-05-30 | Toyo Ink Mfg Co Ltd | Method for producing azo pigment and azo pigment to be obtained thereby |
| CN102585546A (en) * | 2011-12-30 | 2012-07-18 | 山东宇虹颜料有限公司 | Preparation method for C.I. pigment red 53:1 |
| CN102838883A (en) * | 2012-09-25 | 2012-12-26 | 山东宇虹新颜料股份有限公司 | Preparation method for C.I. paratonere 49:1 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113698792A (en) * | 2021-09-10 | 2021-11-26 | 百合花集团股份有限公司 | Preparation method of azo lake organic pigment capable of reducing aromatic amine residues |
| CN113698792B (en) * | 2021-09-10 | 2022-05-10 | 百合花集团股份有限公司 | Preparation method of azo lake organic pigment capable of reducing aromatic amine residues |
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